Structure via PubChem · Public domain (PubChem)
deoxyuridine
Sign in to saveAlso known as 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-2-tetrahydrofuranyl]pyrimidine-2,4-dione, 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione, 1-[(2R,4S,5R)-4-hydroxy-5-methylol-tetrahydrofuran-2-yl]pyrimidine-2,4-quinone, 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione, Deoxyribose uracil, Uracil desoxyuridine, 1-(2-Deoxy-delta-erythro-pentofuranosyl)uracil, Desoxyuridine
Deoxyuridine (dU) is a compound and a nucleoside. It belongs to a class of compounds known as Pyrimidine 2'-deoxyribonucleosides and closely resembles the chemical composition of uridine but without the presence of the 2' hydroxyl group. Idoxuridine and Trifluridine are variants of deoxyuridine used as antiviral drugs. They are similar enough to be incorporated as part of DNA replication, but they possess side groups on the uracil component (an iodine and a CF3 group, respectively), that prevent base pairing. A known use of dU is as a precursor in the synthesis of Edoxudine.
In the Vinony graph
Within Vinony's link graph, deoxyuridine is referenced by 98 other articles, and connects out to deoxyribonucleotide, iodine and chemical compound.
Vinony files it under Chembox image size set, ECHA InfoCard ID from Wikidata and Nucleosides.
Its subject is documented across 18 Wikipedia language editions.
Chemical data
- Formula
- C9H12N2O5
- Molecular weight
- 228.2 g/mol
- IUPAC name
- 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
- SMILES
- C1[C@@H]([C@H](O[C@H]1N2C=CC(=O)NC2=O)CO)O
- InChIKey
- MXHRCPNRJAMMIM-SHYZEUOFSA-N
- XLogP
- -1.6
- Polar surface area
- 99.1 Ų
- H-bond donors
- 3
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
32,237 papers- A chemical method for fast and sensitive detection of DNA synthesis in vivo.Proceedings of the National Academy of Sciences of the United States of America · 2008
- Oxidative Deformylation of the Predominant DNA Lesion 5-Formyl-2'-deoxyuridine.Chemical research in toxicology · 2024
- Structural basis of template strand deoxyuridine promoter recognition by a viral RNA polymerase.Nature communications · 2022
- 5-Propyl-2'-deoxyuridine: a specific anti-herpes agent.Antimicrobial agents and chemotherapy · 1978
- Development of ethynyl-2'-deoxyuridine chemical probes for cell proliferation.Bioorganic & medicinal chemistry · 2016
via PubMed
Wikidata facts
- Mass
- 228.075
Show 6 more facts
- subject has role
- antimetabolite
- chemical formula
- C₉H₁₂N₂O₅
- isomeric SMILES
- C1[C@@H]([C@H](O[C@H]1N2C=CC(=O)NC2=O)CO)O
- canonical SMILES
- C1C(C(OC1N2C=CC(=O)NC2=O)CO)O
- found in taxon
- Streptomyces
- Commons category
- Deoxyuridine
via Wikidata · CC0
~1 min read
Encyclopedic overview
1 sectionsContents
- References
Deoxyuridine (dU) is a compound and a nucleoside. It belongs to a class of compounds known as Pyrimidine 2'-deoxyribonucleosides and closely resembles the chemical composition of uridine but without the presence of the 2' hydroxyl group. Idoxuridine and Trifluridine are variants of deoxyuridine used as antiviral drugs. They are similar enough to be incorporated as part of DNA replication, but they possess side groups on the uracil component (an iodine and a CF3 group, respectively), that prevent base pairing. A known use of dU is as a precursor in the synthesis of Edoxudine.
This compound exists in all living organisms and can become part of DNA in both prokaryotic and eukaryotic cells through two mechanisms. The first is the removal of an amino group from cytosine to result in uracil and the second is the non-intentional incorporation of pyrimidine where thymine belongs in the DNA, resulting in dUMP.
Excerpted from Wikipedia’s “deoxyuridine” article, available under the CC BY-SA 4.0 licence.